During the Boom Times of late ’20-early ’22, we all often confused Taking Risks in hiring … with Just Plain Ignoring Flags.

Great risks to take, IMHE:

  • Been a Director, but never VP.  The best VPs of Sales I’ve hired were Directors of Sales before.  Not ICs, not top reps.  But folks that had built small teams themselves, and were ready to go to the next level.
  • Very smart, but no industry experience.  Everyone over-indexes on industry experience.  The smart ones can pick up what matters in 30-60 days, though.
  • Not perfect background, but showed up incredibly prepared.  Who cares where they went to school if they can crush it.  Even if you are quietly biased here, let it go when they show up incredibly on top of how your business works, and where it should go.  That’s far better in my experience than hiring a random top-tier university grad.
  • Non-traditional educational experience.  See previous point.  A number of my very best hires never finished high school.
  • Someone truly great tells you they are great.  The best folks you know … know the gems.  Even if you can’t quite see it yourself at first blush.

These are risks. Measured risks that you take as a founder.  Flags are different.  Flags can seem like risks if you over-discuss them, but they actually are early signs a hire just won’t work out.  And whatever you see as a flag during the interview process is almost always 10x bigger once they join full-time.

Flags (not Risks) IMHE:

  • Never stayed anywhere for even 18 months.  Everyone wants to give folks a pass here, and for sure, “startup folks” are passionate and often won’t stay 20 years anywhere.  But if they never stayed anywhere for even 24 months?  Personally, I’ve never seen this work out.
  • No research before interview.  “Informational interviews” may make sense at big tech companies.  But at startups?  If the prospective hire hasn’t put in 15-20 minutes of work before the interview, it never works out well.
  • In love with their industry experience.  See above.  Make sure you’d still hire them if they didn’t work there.
  • Salary is their only reason to leave.  Nothing wrong with wanting to be paid fairly!  But when it’s the main reason someone is interviewing, and especially the first thing they bring up, I just find they are leaving for the wrong reason.
  • No good reason to leave.  I’ve learned to just pass when a candidate can’t explain to me why they’d leave their current role.  The best always have a reason.
  • Zero-effort ATS application.  It’s just way too easy to randomly apply to jobs online.  Maybe once you have a full recruiting team, they can parse some of these.  But I never have found these zero-effort applicants to be a great fit.
  • Any inappropriate or sexist comments.  Don’t let it slide.  It’s always much worse later. 
  • Late.  If it matters, you’re never late.  
  • Slow to Follow up.  At least for sales positions, if they are slow to schedule an interview with you, slow to follow-up, etc. … they’ll be even worse with customers.

The truth is, most of us got … a bit desperate in hiring in the Boom. Growth was everywhere in 2021, but talent wasn’t. Even in a distributed world. There was tons of capital, and there were huge plans to hit. And recruiters all told us we had to settle. That everyone great had better offers at better companies. So we excused Flags as … Risks.

Take risks in hiring in a startup. That’s a superpower, taking measured risks. Take someone great, who hasn’t yet had their shot — and give it to them. Watch them fly.

But Flags? Leave those folks to the ones that can hire massive teams.

First Timer image from here

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